195250-21-6Relevant academic research and scientific papers
Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols via an Intramolecular Friedel?Crafts-Type 1,4-Addition: Access to Cannabidiol Analogues
Bryant, Laura A.,Cobb, Alexander J. A.,Johnston, Callum D.,Lees, Nicholas R.,Shankland, Kenneth,Straker, Hannah E.
supporting information, p. 4067 - 4074 (2021/07/20)
The organocatalytic transformation of resorcinols is extremely rare. In this article, we report a highly enantioselective, organocatalytic intramolecular cyclization of these systems by a Friedel–Crafts-type 1,4-addition using a J?rgensen-Hayashi-like organocatalyst with a large silyl protecting group, and show that heat improves reaction yield with virtually no detriment to enantioselectivity. A variety of bicyclic resorcinols were obtained with excellent enantioselectivities (up to 94%). To show the utility of these constructs, and as part of a wider project involving the synthesis of cannabinoid-like compounds, the resorcinol formed was used to generate both ‘normal’ and ‘abnormal’ cannabidiol (CBD) derivatives which were shown to have anticonvulsant activity. (Figure presented.).
Palladium-catalyzed carbonylative cyclization of aryl alkenes/alkenols: A new reaction mode for the synthesis of electron-rich chromanes
Li, Shuang,Li, Fuzhuo,Gong, Jianxian,Yang, Zhen
supporting information, p. 1240 - 1243 (2015/03/14)
The Pd(II)-catalyzed intramolecular carbonylative cyclization reaction of aryl alkenes and aryl alkenols is reported for the synthesis of structurally diverse chromanes. PdCl2(CH3CN)2 was used as the catalyst and CuCl2 as the oxidant under the balloon pressure of CO. The reaction is conducted under mild conditions, and chromane-type esters and lactones can be generated in a highly regio- and stereoselective manner.
The Sharpless asymmetric aminohydroxylation reaction: Optimising ligand/substrate control of regioselectivity for the synthesis of 3- and 4-aminosugars
Bodkin, Jennifer A.,Bacskay, George B.,McLeod, Malcolm D.
supporting information; experimental part, p. 2544 - 2553 (2009/02/02)
An investigation of the factors responsible for the sense and magnitude of regioselectivity in the Sharpless asymmetric aminohydroxylation (AA) has been conducted. Theoretical investigations of ligand-osmium binding geometry and experimental investigation
Intramolecular Photochemical Reactions of Bichromophoric 3-(Alkenyloxy)phenols and 1-(Alkenyloxy)-3-(alkyloxy)benzene Derivatives. Acid-Catalyzed Transformations of the Primary Cycloadducts
Hoffmann, Norbert,Pete, Jean-Pierre
, p. 6952 - 6960 (2007/10/03)
Irradiation of 3-(alkenyloxy)phenols and 1-(alkenyloxy)-3-(alkyloxy)benzene derivatives, at λ = 254 nm in acidic media, yields benzocyclobutenes, 3-alkylphenols, 3-alkylanisols, and 4-alkyl-1,2dialkyloxybenzenes depending on the substitution pattern of the aromatic ring and the olefinic side chain. The final products are derived from an intramolecular [2 + 2] photocycloaddition and acidic rearrangements from a common intermediate.
